Application of chemical cytochrome P-450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathways via an iminium intermediate was written by Masumoto, Hiroshi;Ohta, Shigeru;Hirobe, Masaaki. And the article was included in Drug Metabolism and Disposition in 1991.COA of Formula: C12H18ClNO This article mentions the following:
Oxidations of the piperidine ring by chem. model and liver microsomal systems were investigated with a simple piperidine derivative, N-benzylpiperidine (BP), as the substrate in order to probe the generality and the mechanism of the biotransformation of the piperidine ring. The piperidine ring of BP as well as that of phencyclidine was suggested to be oxidized to a ketone at the β-position in the meso-tetraphenylporphinatoiron(III) chloride system, and the reaction was expected to occur in the liver microsomal system. The β-oxo formation was observed directly in the liver microsomal system, and found to be dependent on cytochrome P 450. Then it was suggested that the piperidine-β-oxo formation was a general oxidation pathway of the piperidine biotransformation. Hydrogen abstraction in the reaction was not a rate-determining step. Therefore, the authors presumed a possible mechanism of β-oxo formation via BP-iminium. From the comparative study on the reactivities of dipropylbenzylamine (DPB) and BP, and the stabilities of iminium (Im+) species of BP and DPB, it was suggested that BP-Im+ was relatively stable and was the most likely precursor of BP-β-oxo. BP-Im+ and its free base, enamine, afforded large amounts of BP-β-oxo as well as BP-α-oxo in the chem. model and the microsomal systems. This evidence supported the iminium-enamine mechanism. In the experiment, the researchers used many compounds, for example, 1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1COA of Formula: C12H18ClNO).
1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.COA of Formula: C12H18ClNO
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem